Stadium: Court 1 Round: 27 Ground: Clay
| Challenger - Florianopolis | 2021/12/07 16:05 | Pedro Boscardin Dias v Gonzalo Villanueva | 6-4,5-7,2-6 |
| ITF - M25 Kiseljak | 2023/06/01 10:55 | Pedro Boscardin Dias v Igor Gimenez | 7-5,6-4 |
| ITF - M25 Kiseljak | 2023/05/31 07:00 | Kacper Zuk v Pedro Boscardin Dias | 2-6,6-7 |
| Challenger Skopje | 2023/05/22 09:00 | Wilson Leite v Pedro Boscardin Dias | 7-6,6-4 |
| Challenger Skopje | 2023/05/21 09:50 | Yanaki Milev v Pedro Boscardin Dias | 2-6,6-7 |
| Challenger - Oeiras | 2023/05/14 14:10 | Manuel Guinard v Pedro Boscardin Dias | 6-2,7-6 |
| Challenger - Coquimbo | 2023/05/03 18:20 | Pedro Boscardin Dias v Joao Lucas Reis da Silva | 2-6,2-6 |
| Challenger - Coquimbo | 2023/05/01 19:35 | Naoki Nakagawa v Pedro Boscardin Dias | 6-4,5-7,3-6 |
| Challenger - Buenos Aires | 2023/04/25 13:00 | Pedro Boscardin Dias v Hernan Casanova | 1-6,3-6 |
| ITF - M25 Kiseljak | 2023/06/01 08:55 | Samuel Puskar v Gonzalo Villanueva | 3-6,4-6 |
| ITF - M25 Kiseljak | 2023/05/31 11:50 | Corey Gaal v Gonzalo Villanueva | 5-7,2-6 |
| Challenger Skopje | 2023/05/21 09:00 | Gonzalo Villanueva v Mathias Bourgue | 2-6,2-6 |
| Challenger - Coquimbo | 2023/05/01 16:55 | Murkel Dellien v Gonzalo Villanueva | 6-3,6-4 |
| Challenger - Buenos Aires | 2023/04/28 15:35 | Andrea Collarini v Gonzalo Villanueva | 6-2,6-1 |
| Challenger - Buenos Aires | 2023/04/26 14:30 | Gonzalo Villanueva v Nick Hardt | 7-5,1-6,7-5 |
| Challenger - Buenos Aires | 2023/04/24 18:05 | Gonzalo Lama v Gonzalo Villanueva | 6-7,6-7 |
| Challenger - Florianopolis | 2023/04/19 14:40 | Gonzalo Villanueva v Guido Ivan Justo | 3-6,7-6,2-6 |